Anthraquinone dye and process of making same.



NO. 778,036. Patented December 20, 1904.

UNITED STATES PATENT OFFICE.

EDUARD HEPP, OF FRANKFORT-ON-THE-MAIN, AND RUDOLF UHLENHUTH,

OF HOOHST-ON-THE-MAIN, GERMANY, ASSIGNORS TO FARBWVERKE, VORM. MEISTER, LUCIUS 8: BRUNING, OF HOOHST-ON-THE-MAIN, GER- MANY, A CORPORATION OF GERMANY.

ANTHRAQUINONE DYE AND PROCESS OF MAKING SAME.

SPECIFICATION forming part of Letters Patent No. 778,036, dated December 20, 1904.

Application filed June 2'7, 1904. Serial No. 214,272. (Specimens) T all whom it y Con/067%" The new dyestuff sulfonic acids represent Be it known that we, EDUARD HEPP, Ph. D., when dry and pulverized dark-green powders residing at Frankfort-on-the-Main, and RU- very easily soluble in water, the aqueous solu- 5 DOLFUHLENHUTH, Ph. D., residing at Hochsttion remaining unchanged on adding sodium 5 on-the Main,Germany, chemists, both citizens carbonate, but turning somewhat more bluish of the Empire of Germany, have invented a on adding caustic alkali. They dye unmorcertain new and useful Anthraquinone Dyedanted and chrome-mordanted wool and stuff, of which the following isa specification. chrome-mordanted cotton green shades very 55 Our invention relates to the production of fast to light acids and alkalies.

IO new green dyestuffs by acting with sulfonat- To carry out our process, we proceed, for ingagentson1.A-dialphylido-5-oxy-anthraquiinstance, as follows: nones having the general formula Example: Ten kilos of 1.4.5-trioxy-anthraolrr nHR quinone hydrid are heated with sixty kilps of 60 O0 para-toluidin and ten ki os of boric acic for about two hours to 115 centigrade. The mass I l I still Warm is diluted with methyl alcohol, the v I separated product of condensation is filtered,

\ washed with alcohol, and dried. It represents 5 CO 1 blue-black needles of metallic luster melting at I NHR 239 centigrade. It is soluble with great difin which "R represents an aromatic radical, ficulty in indifferent solvents,soluble in alcohol such as phenyl, tolyl, xylyl, and the like. in presence of alkalies witha green-blue color.

The said dialphylido-oxy-anthraquinones In concentrated sulfuric acid it yields a blue 7 may be prepared by condensing 1.4. 5-trioxysolution which on being diluted with water beanthraquinone hydrid with aromatic amins in comes green, a green precipitate being sepapresence of the oxygen of the air, the trioxyrated. anthraquinone hydrid being obtained, for in- To manufacture the sulfonic acid, one part, stance, as follows: The 1.5 and 1.8-nitroanby weight, of 1.4di-para-toluido-5-ox *-an 75 tlnaquinone-sulfonic acids are transformed thraquinone is introduced at ordinary teminto the corresponding methoxyanthraquiperature into ten parts, by weight, of fuming none-sulfonic acids by means of a solution sulfuric acid containing five per cent. of anhyof caustic alkalies in methyl alcohol. These drid and the mixture is allowed to stand unmethoxyanthraquinone-sulfonic acids are then til a test portion diluted with water gives no 30 converted into the 1.4.5-trioxy-anthraquinone precipitate. The mass is then poured into 3 5 by nitrating them, reducing the products thus Water, the sulfuric acid is eliminated with hyobtained, and heating under pressure the cordrate of lime, and the sodium salt obtained in responding amidooxy anthraquinonesulthe usual manner is evaporated to dryness.

fonic acids in a closed vessel with hydrate of It is a green powder readily soluble in water 5 lime. By heating the trioxy-anthraquinone with a green color, dyeing unmordanted wool with stannous chlorid and crystallizing the green shades of remarkable fastness to light product from benzene the trioxy-anthraquiand alkali. Other of the above-defined 1.4- none hydrid is obtained in the shape of orange dialphylido- 5 oxyanthraquinones are transred prisms soluble in concentrated sulfuric formed in a similar manner into the corre- 9 acid with a yellow color and melting at 210 sponding sulfonic acids.

centigrade. It is soluble in dilute caustic Having now described our invention, what alkalies with a yellow color which becomes we claim is violet by the oxygen of the air. 1. The process for producing new anthraquinone dyestuffs, which consists in treating 1. l-dialphyl1d0-5-oxy-anthraqumones having the general formula:

/NHR 1 c rrrp m-na 4 on 5 wherein R represents an aromatic radical,

- such as phenyl, tolyl, Xylyl and the like, with suli'onating agents.

2. The process for producing a new anthraquinone dyestuif, which consists in treating 1.4-di-para-toluido-5-oXy-anthraquinone having the formula:

u i ig g liilg with sulfonating agents.

3. The herein-described new anthraquinone dyestuffs, obtainable by sulfonating lit-dialphylido 5 oXy anthraquinones having the general formula:

NHR

l I be) ,2

NHR

which dyestuffs, when dry and pulverized, are green powders, soluble in water with a green color, dyeing unmordanted and chrome-mordanted wool and chrome-mordanted cotton green shades, very fast to light, acids and alkalies.

L. The herein-described new anthraquinone dyestuff, obtainable by sulfonating 1.4-dipara-toluido-5-oXy-anthraquinone, having the formula H NHC7H7 EDUARD HEPP. RUDOLF UHLENHUTH.

WVitnesses:

J OI-IANN HARTENSTEIN, JOSEPH BLACK. 

